Journal
ORGANIC LETTERS
Volume 18, Issue 4, Pages 720-723Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03698
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Funding
- Natural Sciences and Engineering Research Council of Canada
- JSPS
- Grants-in-Aid for Scientific Research [15J04272] Funding Source: KAKEN
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We report the first examples of straightforward trans-hydroboration of internal alkynes at room temperature with 9-BBN, producing five-membered BN-heterocycles. Contrary to conventional cis-hydroboration, we demonstrate that the introduction of a pyridyl group switches the stereoselectivity of the reaction. A hydride migration mechanism has been proposed and supported by DFT calculations for the trans-hydroboration. This new hydroboration approach allows facile construction of new blue fluorescent BN-heterocyclic compounds.
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